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Copper‐Catalyzed ortho ‐Functionalization of Quinoline N ‐Oxides with Vinyl Arenes
Author(s) -
Hu Hui,
Hu Xiaoping,
Liu Yuanhong
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007699
Subject(s) - quinoline , chemistry , regioselectivity , pinacol , alkylation , nucleophile , copper , catalysis , medicinal chemistry , polymer chemistry , organic chemistry , combinatorial chemistry
An efficient copper‐catalyzed regioselective C−H alkenylation and borylative alkylation of quinoline N ‐oxides with vinyl arenes in the presence of pinacol diborane has been developed. The reaction proceeds through the borylcupration of the vinyl arenes followed by nucleophilic attack of the resulting alkyl copper species to the quinoline N ‐oxides. Benzoquinone and KO t Bu were identified as the necessary additives at the second step of the reaction that are crucial for the success of the reaction. A wide range of C2‐functionalizaed quinolines were obtained with good functional group tolerance, which may find utilities in pharmaceuticals and synthetic chemistry.